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Usage

Uses

Used in Pharmaceutical Industry:
R(-)-GAMMA-VINYL GABA is used as an antiepileptic drug for the treatment of various types of epilepsy, including complex partial seizures and infantile spasms. It works by irreversibly inhibiting the enzyme GABA transaminase, leading to an increase in GABA levels in the brain and reducing seizure activity.
R(-)-GAMMA-VINYL GABA is also used as an antidepressant, antipsychotic, and anxiolytic due to its potential effects on neurotransmitter levels and modulation of neuronal activity. This makes it a promising candidate for the treatment of mood disorders, psychotic disorders, and anxiety disorders.

InChI:InChI=1/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

Upstream product

• 93288-24-5 (R)-5-vinyl-2-pyrrolidinone 
• 7529-16-0 5(S)-Vinyl-2-Pyrrolidinone 
• 148073-34-1 (S)-ethyl 4--5-hexenoate 
• 151929-39-4 ethyl (4S)-4-(benzyloxycarbonylamino)-6-methylthio-2-hexenoate 
• 151929-45-2 (5R)-5-(2-methylthioethyl)-2-pyrrolidinone 
• 330851-14-4 (R)-4-tert-Butoxycarbonylamino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 210415-79-5 (S)-4-(Benzyl-hydroxy-amino)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-ynoic acid methyl ester 

Relevant academic research and scientific papers

Scalable Synthesis of Both Enantiomers of Vigabatrin, an Antiepileptic Drug

Vigabatrin is a potent inhibitor of gamma-aminobutyric acid (GABA) catabolism used for the treatment of epilepsy. Here we have synthesized both enantiomers of the drug vigabatrin in five steps from known intermediates using Wittig olefination and pyrolytic elimination as key steps. The target compounds are synthesized in gram scale amounts with >98 % enantiopurity.

Resolution of racemic Vigabatrin using tartaric acid

An efficient and simple resolution methodology for the preparation of (S)- and (R)-Vigabatrin has been developed. In addition, a method of preparation for the novel compounds Vigabatrin-l-tartarate and Vigabatrin-d-tartarate is also described. The title c

Catalytic asymmetric intramolecular aminopalladation: Enantioselective synthesis of vinyl-substituted 2-oxazolidinones, 2-imidazolidinones, and 2-pyrrolidinones

A new catalytic asymmetric synthesis of five-membered nitrogen heterocycles is reported. This synthesis employs ferrocenyloxazoline palladacycles (FOP trifluoroacetate catalysts) 2 and 4 and proceeds by a catalytic cycle involving Pd(II) intermediates. Fo

A short synthesis of γ-amino acids from nitrones; synthesis of Vigabatrin

Treatment of the γ-N-hydroxylamino-α,β-acetylenic esters, obtained by the reaction of nitrones with alkyl 3-lithiopropiolates, with H2 over Raney nickel, followed by in situ protection of the formed amines, gives N-Boc-γ-amino esters. This meth

Asymmetric Synthesis of Both Enantiomers of Vigabatrin: An Approach Using Methionine as the Chiral Pool

Both enantiomers of the potent GABA-T inhibitor, 4-amino-5-hexenoic acid (2), were prepared in five steps from (R)- or (S)-methionine using a one-pot reduction-homologation of an α-amino ester as the key reaction step.

Synthesis of optically pure mechanism-based inhibitors of γ aminobutyric acid aminotransferase (GABA-T) via enzyme-catalyzed resolution

The kinetic resolution of γ-ethynyl-,γ-allenyl- and γ-vinyl GABA was accomplished by penicillin acylase-catalyzed hydrolysis of their N-phenylacetyl derivatives. The procedure employs inexpensive commercially available immobilized enzyme.